Potassium Carbonate → (3-Cyclopent-1-enyl-imidazo[1,2-b]pyridazin-6-yl)-[2-(2-ethoxy-phenyl)-ethyl]-amine

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Reaktionsgleichung

Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH2:21][CH3:22])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[C:23]1(B2OC(C)(C)C(C)(C)O2)[CH2:27][CH2:26][CH2:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:23]1([C:2]2[N:6]3[N:7]=[C:8]([NH:11][CH2:12][CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[O:20][CH2:21][CH3:22])[CH:9]=[CH:10][C:5]3=[N:4][CH:3]=2)[CH2:27][CH2:26][CH2:25][CH:24]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

A mixture of (3-bromo-imidazo[1,2-b]pyridazin-6-yl)-[2-(2-ethoxy-phenyl)-ethyl]-amine (90 mg, 0.25 mmol), 2-cyclopent-1-enyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (97 mg, 0.5 mmol), K2CO3 (104 mg, 0.75 mmol) and dichlorobis(triphenylphosphine)palladium(II) (8.8 mg, 0.013 mmol) in MeCN/water (2.8 ml/0.7 ml) was heated in a microwave at 150° C. for 15 min. The water layer was removed and the organic layer was concentrated. The residue was subjected to ISCO. The product was further purified by preparative to give the titled compound (60 mg).

Aufarbeitung

customThe water layer was removed
concentrationthe organic layer was concentrated
customThe product was further purified by preparative

Quellen und Nachweise

ORD-Eintrag: ord-43d1c7a61666407986cd97d54bbe0031
Quelldatensatz: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08969565B2

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